Cabin in the Woods

Finally, I get to give you another TRUE story after a WAY too long 'dry spell'. This story is completely true (and may be a little boring maybe...would love any feedback). Only the names have been changed to blah blah blah...

Anyone who is familiar with my writings knows my stories are true and not made up unless I openly state at the beginning that it's a piece of fiction. This is not fiction, this story is true and happened very recently. And I couldn't wait to tell you about it. It's been way too long since the last time I had sex as a 'woman' (I'm a crossdresser, duh), over 1 1/2 years. Here goes...

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I have been trying to find a man to fuck me while I'm crossdressed for what seems like forever. Craigslist is about the best option for this, but while it may be the BEST option, it's not necessarily a great one. Fakes and phonies and game players abound. No shortage of idiots, that's for sure. My last real-life encounter had been the guy in his wife's minivan (you probably read that story if you're familiar with me), which happened September of '14. Here we are in July of '15 and I'm still looking for another. Many many blow offs, rejections, and jerk-arounds. But finally...I got a hit.

I got a reply to my ad from what seems to be a nice guy, an older guy, who's wife left him recently. My ad stated I was a full crossdresser (semi-passable now, with wig and getting pretty good at makeup), and that I was seeking a top to fuck me, preferably bareback if we were both comfortable with it. I LOVE cum running out of my ass for the rest of the night! We get to talking and he SEEMS genuine. (I won't get into boring details in the story but it turns out we were both recently tested for STD's and both are STD free).

We agreed to meet up one night when I could get out dressed. Now, my wife knows I dress and like to go out driving around late at night, but I still like to get out unnoticed, that gives me more time and arouses less suspicion. I pick a night when my wife went to bed earlier than usual, and the preparation began. Anyone else who does what I do KNOWS the feeling of preparing for a sex hookup...you're horny, nervous, scared, excited, happy, thrilled, and you constantly have second thoughts and sometimes you might act on your second thoughts and back out (I don't once I commit). It's a very anxious experience, much more so than a guy meeting a chick...cuz this time you're a guy in women's clothes out in public meeting another guy...and that COULD end badly. But then you think about the pleasure, the joy, the gratification, the feeling of being a woman for a short time and pleasing a man while feeling him inside you, the immense pleasure you will get from that, and caution gets thrown to the wind. And you go for it.

It's about 11 pm. I start with a touch-up shave of my face, close as I possibly can, legs, pits, chest and my ass, as good as I can get with not being able to see it. Then for whatever reason, perhaps a little 'rusty' or just overly excited, I start my makeup FIRST instead of dressing first. No big deal, I just don't like to mess up my makeup by pulling on a top or a dress. But it worked out in the end. I start with the foundation, a Q-tip loaded with a glob placed in numerous spots around my face...dip it in, place on face and so on. Then with my hands I blend it in, all over from my forehead to my neck. Gotta admit, I'm getting fairly good at this, and it definitely transforms me from an overweight middle-age man to a slightly overweight but hot semi-passable crossdresser. Seriously, you'd have to get close to tell I was a man. The foundation effectively covers what no razor can get, but it's obviously not a natural look, so I follow this with a flesh-colored powder, matching my skin tone. After blending that with the powder brush, I brush on some blush, followed by eye shadow and a bright red lipstick. Wow, I am really looking pretty good! Now...the clothes!

I chose an all-black outfit, as I usually do. Rarely do I wear any colors. Black works every time in any situation at any time of day or season. And I don't have many colored clothes anyways. I started with my belly cincher, basically a slip-on tight thing that sucks in my belly quite a bit, not unlike a corset but with no strings or zippers. I already have on a pair of lace purple panties (only colorful articles of clothing I routinely wear are my panties), and pull on a sheer pair of black pantyhose. I prefer pantyhose over stockings, I just love the total coverage, the feeling, and they can easily be converted to crotchless...if you know what I mean.

I had just bought a nice new top that very day, so I pulled that on, careful not to mess up my makeup. This I followed with a black body-contour skirt that hugs your curves and just looks damn hot! Real women look phenomenal in this type of skirt, and I held my own, looking pretty damn good myself! I then strapped my 4" strapped-wedges on, a gold ankle bracelet, and my clip-on earrings, then combed out my wig, and adjusted it on my head until it was right where it should be. It's an auburn color, and comes down just below the shoulders.

This will be a 'christening' of sorts, the first time ever getting fucked FULLY dressed with wig and makeup, and the first time for this outfit, I like to wear something I've never been fucked in each time. I touched up my lipstick and lubed up my ass real good. Grabbed my purse containing my license (just in case), my phone, keys and my lipstick and the small bottle of lube, and out the door I went! I had disabled the outside motion-sensor light on the garage as I park outside during the summer, we fix up the garage and have a screen garage door. It's late and all my neighbors turn in early, so it's unlikely I'd be seen...but I do what I can to reduce that chance as much as possible.

I follow the directions to his place, a year-sound cabin in the woods, about 15 minutes from my house. After arriving, he greets me at the door and we go into his cabin. It's pretty nice, nothing really fancy but what would anyone expect from a cabin that didn't cost a million dollars? On his wall hangs a huge flat-screen TV, a porn scene playing from a DVD. We sit next to one another on the couch, watching the video for a few minutes until he is hard as a rock! He had told me he might have a problem getting hard, but I guess I must have had some effect on him. This would be his first ever bisexual encounter, claiming he'd never done this before.

He exclaims he is hard, somewhat surprised in himself, and asks me to sit on him. Well, I'm only too happy to oblige! I stand up, lift my skirt and lower my pantyhose just below my ass, then I straddle him with my back to him and lower myself onto one of the thickest cocks I have ever had the pleasure of having inside me! Thick as a beer bottle! It enters my hole with ease, as I was well lubed and I'm used to big cocks and dildos. He may not have been LONG, (but long enough), but THICK! That stretch! Oh fuck...that feeling of my hole spreading open as my insides stretch to accommodate this beautiful cock! That unbeatable feeling of sliding up and down...I'm getting fucked! I'm getting laid like a woman...we're both getting laid! Sex. The feeling of sex...dirty, forbidden sex...is like no other feeling! I'm balancing myself on his knees as I bounce up and down on his cock. It's amazing...simply amazing. I like hung guys, and while not 'hung' in the traditional definition, this is a dream-dick!

After a while we switch positions, I lean over the armrest of the couch, and he moves in from behind. Again he penetrates, the best part of the sex. It pops in and he once again is pumping me, pleasing himself, pleasing ME. He bangs the fuck out of me longer than anyone else ever has, though it's NEVER long enough! His hands on my hips, my ass in the air, one pantyhosed legs on the floor for balance, the other between the couch cushion and the back, my hands holding onto the armrest like I was on a roller coaster. That wonderful beer-bottle cock assaulting my love hole with a purpose...and that purpose came with a loud moan followed by heavy breathing.

He came inside of me. I could feel his cum coming out, even though he was still in me. When he does pull out, I could hear a liquidy 'pop' as he does...and I feel his cum slowly running down my crack toward my own anatomy. The deed was done. He came, I didn't. I didn't need to. MY pleasure comes from the feeling of getting fucked, from giving a man what his woman won't, while wearing what a woman won't anymore. If not for crossdressers, the women's clothes and shoes manufacturers would be out of business. I usually jerk off right after I get fucked, but I don't do that this night, I'll wait til I get home.

I pull my pantyhose up and my skirt down. We have a drink, and I get up to leave. We both want a regular thing, and I have finally found one. So close to home is the biggest factor that makes this even possible. The less time away from home, the less likely it will arouse any suspicion. I grab my purse and get in my car to drive home. Once home, I lie back on my bed and close my eyes, grab my own cock, and relive the night I just had. The next time will be soon. I won't bother writing about it unless something very different transpires, but I can tell you one thing...that next time can't come fast enough!